methyl 3-amino-2,2-dimethyl-3-(4-methoxyphenyl)propanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 3-amino-2,2-dimethyl-3-(4-methoxyphenyl)propanoate
• 英文别名: methyl 3-amino-3-(4-methoxyphenyl)-2,2-dimethylpropanoate
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: ATIJOZTYOWYFES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-amino-2,2-dimethyl-3-(4-methoxyphenyl)propanoate 在 甲基溴化镁 作用下， 以 乙醚 为溶剂， 反应 48.0h， 生成 3,3-dimethyl-4-(4-methoxyphenyl)-azetidin-2-one
  参考文献：
  名称：

  Preparation of β-Amino Esters and β-Lactams from Nitriles via Aldimine-Borane Complexes

  摘要：

  A one-pot synthesis of beta-amino esters has been achieved in 59-75% yield from aromatic and aliphatic nitrites via the condensation of the corresponding non-enolizable and enolizable aldimine-triethylborane complexes, respectively with methyl trimethylsilyl ketene acetals. Grignard-mediated lactamization of the intermediate beta-amino esters provides the corresponding beta-lactams in the same pot in 58-74% overall yield.

  DOI：

  10.3987/com-10-s(e)95
• 作为产物：
  描述：

  4-甲氧基苯甲腈 在 zinc(II) iodide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 5.0h， 生成 methyl 3-amino-2,2-dimethyl-3-(4-methoxyphenyl)propanoate
  参考文献：
  名称：

  Preparation of β-Amino Esters and β-Lactams from Nitriles via Aldimine-Borane Complexes

  摘要：

  A one-pot synthesis of beta-amino esters has been achieved in 59-75% yield from aromatic and aliphatic nitrites via the condensation of the corresponding non-enolizable and enolizable aldimine-triethylborane complexes, respectively with methyl trimethylsilyl ketene acetals. Grignard-mediated lactamization of the intermediate beta-amino esters provides the corresponding beta-lactams in the same pot in 58-74% overall yield.

  DOI：

  10.3987/com-10-s(e)95

文献信息

• Lewis Acid Mediated Addition of Silyl Ketene Acetals to Sulfinimines
  作者：Robert Kawecki

  DOI：10.1021/jo990913f

  日期：1999.11.1
• Preparation of β-Amino Esters and β-Lactams from Nitriles via Aldimine-Borane Complexes
  作者：P. Veeraraghavan Ramachandran、Debanjan Biswas、Guang-Ming Chen

  DOI：10.3987/com-10-s(e)95

  日期：——

  A one-pot synthesis of beta-amino esters has been achieved in 59-75% yield from aromatic and aliphatic nitrites via the condensation of the corresponding non-enolizable and enolizable aldimine-triethylborane complexes, respectively with methyl trimethylsilyl ketene acetals. Grignard-mediated lactamization of the intermediate beta-amino esters provides the corresponding beta-lactams in the same pot in 58-74% overall yield.